Organo-Photoredox Catalyzed Synthesis of Phenanthrene

Kumari, Nidhi (2021) Organo-Photoredox Catalyzed Synthesis of Phenanthrene. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS Dissertation of Nidhi Kumari (16MS086)) 16MS086_Thesis_file.pdf - Submitted Version Restricted to Repository staff only Download (3MB)

Abstract

Phenanthrenes are the important class of polycyclic aromatic hydrocarbon (PAH) which have potential use in synthesizing dyes, plastics and pesticides, explosives and drugs (steroids, resin acids, morphine, and alkaloids). Hence, the preparation of phenanthrene has attracted our considerable interest of organic chemists. A transition metal and oxidant or reductant-free approach has been developed en route to access of phenanthrenes at mild condition. The reaction occurs at room temperature utilizing Acridine Orange Base (AOB) as the organophotoredox catalyst. The catalyst shows an adequate triplet excited-state lifetime of 1359 ns and therefore, displays a dual role of photo-induced isomerization as well as deaminative annulation via photoreduction and thereby aromatization in presence of visible-light of proper wavelength. This organo-photoredox method demonstrates a great functional group tolerance with a broad diversity of substrates in good to excellent yields. Electrochemical and photophysical studies have been carried out to establish the mechanism.

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